ethyl (R)-5-acetoxycyclopent-1-enecarboxylate | 143168-16-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (R)-5-acetoxycyclopent-1-enecarboxylate
• 英文别名: ethyl 5(R)-acetoxy-1-cyclopentenecarboxylate；ethyl (5R)-5-acetyloxycyclopentene-1-carboxylate
• CAS: 143168-16-5
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: ZRBIIJNQSLHRAQ-SECBINFHSA-N

物化性质

• 沸点：
  256.2±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (R)-5-acetoxycyclopent-1-enecarboxylate 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 氯化亚砜 、 ammonium acetate 、 氢气 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 生成 2-[(1S,2S)-2-(3-Methoxy-benzyl)-cyclopentyl]-4,5-diphenyl-oxazole
  参考文献：
  名称：

  Replacing the cyclohexene-linker of FR181157 leading to novel IP receptor agonists: Orally active prostacyclin mimetics. Part 6

  摘要：

  The synthesis and biological activity of novel derivatives of our previously reported IP receptor agonist FR181157 is described. SAR studies to replace the cyclohexene-linker of FR181157 led to the discovery of compound 1i (FR207845) as a potent non-prostanoid PGI(2) mimetic with good oral bioavailability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.076
• 作为产物：
  描述：

  乙基5-羟基-1-环戊烯-1-羧酸酯 以50%的产率得到ethyl (R)-5-acetoxycyclopent-1-enecarboxylate
  参考文献：
  名称：

  Resolution and Utilization of Ethyl 5-Hydroxycyclopent-1-enecarboxylate: Enantioselective Synthesis of (+)-Mitsugashiwalactone and (-)-Dolichodial

  摘要：

  光学纯的乙基5-羟基环戊-1-烯羧酸酯已通过脂肪酶介导的动力学分辨率，从外消旋乙基5-羟基环戊-1-烯羧酸酯中以优异的光学产率获得其醋酸酯的两种对映异构体。因此获得的光学纯（R）对映体已转化为两种天然存在的紫杉醇单萜，(+)-三叶紫杉醇内酯和(-)-多利克醛。

  DOI：

  10.1055/s-1995-3930

文献信息

• 4,5-diaryloxazole derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06025375A1

  公开（公告）日：2000-02-15

  Heterocyclic compounds of the formula: ##STR1## whereinR.sup.1 is carboxy or protected carboxy, R.sup.2 is aryl which may have suitable substituent(s), R.sup.3 is aryl which may have suitable substituent(s), A.sup.1 is lower alkylene, A.sup.2 is bond or lower alkylene and -Q- is ##STR2## etc., and pharmaceutically acceptable salts thereof which are useful as a medicament.

  式子为：##STR1##的杂环化合物，其中R.sup.1是羧基或保护羧基，R.sup.2是含有适当取代基的芳基，R.sup.3是含有适当取代基的芳基，A.sup.1是低碳链，A.sup.2是键或低碳链，-Q-是##STR2##等，以及与药学上可接受的盐，可用作药物。
• Enantiocomplementary synthesis of functionalized cycloalkenol building blocks using lipase
  作者：Seiichi Takano、Takahiro Yamane、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1016/s0957-4166(00)82178-3

  日期：1992.7

  Racemic 2-carbethoxy-2-cyclopenten-1-ol [(+/-)-3a] and racemic 2-carbethoxy-2-cyclohexen-1-ol [(+/-)-3b] afforded the corresponding (R)-acetates [(R)-4a and (R)-4b] leaving the corresponding (S)-alcohols [(S)-3a and (S)-3b] unchanged upon treatment with vinyl acetate in tert-butyl methyl ether in the presence of lipase PS, respectively, while the racemic acetates [(+/-)-4a and (+/-)-4b], derived from racemic precursors, (+/-)-3a and (+/-)-3b, on suspension with lipase in a phosphate buffer solution afforded the corresponding (R)-alcohols [(R)-3a and (R)-3b] leaving the corresponding (S)-acetates [(S)-4a and (S)-4b] unchanged, respectively.
• Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis
  作者：Enikő Forró、Zsolt Galla、Ferenc Fülöp

  DOI：10.1016/j.molcatb.2013.09.024

  日期：2013.12

  The ester function of ethyl cis-(+/-)-2-hydroxycyclopentane-1-carboxylate [(+/-)-1] and ethyl (+/-)-5-hydroxycyclopent-1-enecarboxylate [(+/-)-2] was demonstrated to undergo hydrolysis, as a side-reaction, during asymmetric (E > 200) O-acylation with Candida antarctica lipase B (CAL-B) as catalyst and vinyl acetate as acyl donor in t-BuOMe at 30 degrees C. This competition of acylation and undesirable hydrolysis draws attention to CAL-B-catalyzed non-hydrolytic resolutions where the substrates contain any hydrolysable functions. Enantiomerically enriched cis-2-hydroxycyclopentane-1-carboxylic acid (ee = 90%) and 5-hydroxycyclopent-1-enecarboxylic acid (ee = 47%) were prepared through de nova CAL-B-catalyzed hydrolysis of (+/-)-1 and (+/-)-2 with added H2O in t-BuOMe at 30 degrees C. (C) 2013 Elsevier B.V. All rights reserved.
• Yamane, Takahiro; Ishizaki, Michiyo; Suzuki, Mahito, Heterocycles, 1996, vol. 42, # 1, p. 65 - 69
  作者：Yamane, Takahiro、Ishizaki, Michiyo、Suzuki, Mahito、Takahashi, Michiyasu、Hiroya, Kou、Takano, Seiichi、Ogasawara, Kunio

  DOI：——

  日期：——
• 4,5-DIARYLOXAZOLE DERIVATIVES
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0736018B1

  公开（公告）日：2000-07-05